CHEBI:76293 - azadirone

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ChEBI Name azadirone
ChEBI ID CHEBI:76293
Definition A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by an oxo group at position 3, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antiplasmodial and antineoplastic activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H36O4
Net Charge 0
Average Mass 436.58300
Monoisotopic Mass 436.26136
InChI InChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/m0/s1
InChIKey XXIKKMLIDXLAIK-RFKFVWFBSA-N
SMILES CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)c1ccoc1
Roles Classification
Biological Role(s): antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
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ChEBI Ontology
Outgoing azadirone (CHEBI:76293) has role antineoplastic agent (CHEBI:35610)
azadirone (CHEBI:76293) has role antiplasmodial drug (CHEBI:64915)
azadirone (CHEBI:76293) has role plant metabolite (CHEBI:76924)
azadirone (CHEBI:76293) is a acetate ester (CHEBI:47622)
azadirone (CHEBI:76293) is a cyclic terpene ketone (CHEBI:36130)
azadirone (CHEBI:76293) is a furans (CHEBI:24129)
azadirone (CHEBI:76293) is a limonoid (CHEBI:39434)
azadirone (CHEBI:76293) is a tetracyclic triterpenoid (CHEBI:26893)
Incoming 20,21,22,23-tetrahydro-23-oxoazadirone (CHEBI:67291) has functional parent azadirone (CHEBI:76293)
IUPAC Name
(5α,7α,13α,17α)-17-(furan-3-yl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl acetate
Registry Numbers Types Sources
25279-67-8 CAS Registry Number ChemIDplus
4214438 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14592518 PubMed citation Europe PMC
1593280 PubMed citation Europe PMC
16401554 PubMed citation Europe PMC
17917286 PubMed citation Europe PMC
20669933 PubMed citation Europe PMC
24075352 PubMed citation Europe PMC
24078627 PubMed citation Europe PMC
Last Modified
09 January 2014